Isobutyl iodide → HCID 59441661, compound

HRID 1014207Notes

Reaction equation

HRID 1014207 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH3:18][CH:19]([CH3:22])[CH2:20]I.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:22])[CH3:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 39674091-(3-Methoxy-4-nitrophenyl)piperazine

Product 1

HCID 59441661HCID 59441661, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[3-(methyloxy)-4-nitrophenyl]piperazine (2.09 g, 8.44 mmol), 2-methyl-iodopropane (2.1 g, 11.39 mmol), and potassium carbonate (4.7 g, 34 mmol) in acetonitrile (80 mL) was heated in a pressure vessel at 80° C. for 24 hours. The reaction was cooled and the acetonitrile was removed under reduced pressure. The solids were dissolved in methylene chloride/water. The organic layer was dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. The resultant residue was purified by chromatography on SiO2 (10% MeOH/CH2CL2 with 0.2% NH3) to give 1-[3-(methyloxy)-4-nitrophenyl]-4-(2-methylpropyl)piperazine as a pale yellow solid (1.70 g, 5.8 mmol, 69% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.91 (d, J=6.59 Hz, 6 H), 1.80 (ddd, J=13.69, 7.05, 6.91 Hz, 1 H), 2.13 (d, J=6.04 Hz, 2 H), 2.52 (s, 4 H), 3.38 (s, 4 H), 3.93 (s, 3 H), 6.29 (d, J=2.38 Hz, 1 H), 6.40 (dd, J=9.43, 2.47 Hz, 1 H), 7.98 (d, J=9.52 Hz, 1 H).

Workup

  1. temperatureThe reaction was cooled
  2. customthe acetonitrile was removed under reduced pressure
  3. dissolutionThe solids were dissolved in methylene chloride/water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe resultant residue was purified by chromatography on SiO2 (10% MeOH/CH2CL2 with 0.2% NH3)

Sources & evidence

ORD record
ord-6ef00b16bdd94e3689873e9999542bbd
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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